2000: The antitrust trial sets the background

The antitrust case brought by the United States government against Microsoft was filed in 1998. In mid-2000, Judge Thomas Penfield Jackson ruled against the company and ordered that it be broken up. An appeals court upheld the verdict but reversed the penalty portion a year later and handed the case to a new judge. Days after Windows XP shipped, the company agreed to settle the case. The resulting consent decree influenced the development of Windows for the next decade.

2001: Windows XP ships

The revolutionary part of Windows XP was that it unified the business and consumer versions of Windows in a single product. The Windows NT kernel replaced the old DOS-plus-Windows hybrid that had been used in Windows 95, Windows 98, and the ill-fated Windows Millennium Edition. Business users who had adopted the NT-based Windows 2000 a year earlier saw the garish new XP interface, which was widely panned for its "Fisher-Price" appearance. In its first year on the market, XP was far from successful, with less than 10 percent of the installed base upgrading in that first year.

XP's launch event took place in a somber New York City, the month after the 9/11 attacks.

2002: The era of Trustworthy Computing begins

Windows XP had been on the market for only a few months when Bill Gates distributed his now-famous Trustworthy Computing memo. The rise of the Internet had painted a giant target on Windows, and criminals had been successful in exploiting the server version of Windows in 2001 with two devastatingly damaging worms, Code Red and Nimda. As Microsoft's Michael Howard noted a decade later, "His memos are rare, and this one signaled the start of something big within the company."

Gates's memo basically halted all new development and sent every developer at Microsoft back to square one for security training. Windows security headaches continued for the next few years; building security into the core of Windows profoundly affected the development process for the next five years.

2003: The dawn of Patch Tuesday

The security problems that had plagued Windows XP at its launch continued in summer of 2003 with a widespread malicious software attack called MSBlast/32 (aka Blaster). It spread over networks using the RPC protocol and caused affected computers to go into a spontaneous reboot loop. In October of that year, Microsoft made the controversial decision to release updates on a regular schedule. The second Tuesday of each month became known as Patch Tuesday. Instead of scrambling to install updates as soon as they arrived, enterprise customers could plan updates for a regular window each month.

2004: Windows XP Service Pack 2 arrives

In the wake of multiple security problems, Microsoft had focused all its efforts on re-engineering its development process, leading to a new way of designing software and writing code: the Security Development Lifecycle. Windows XP Service Pack 2, code-named "Springboard," was one of the first products to come out of that initiative. As Jim Allchin told Mary Jo Foley, this could easily have been a separate Windows release instead of just a service pack. The decision to release it as a free service pack was a deliberate one, designed to get its significant improvements on as many desktops as possible, as quickly as possible.

And as I noted a few years later, many one-time critics decided by this time that "the interface wasn’t so bad after all (and if you really hated it you could make it look just like Windows 2000)."

2005: The Longhorn Reset

Microsoft had big plans for the successor to Windows XP. It was code-named "Longhorn," and it was filled with "gee golly whiz" features that were going to take the world of personal computing by storm. Longhorn made a big splash at the 2003 Professional Developers Conference (PDC) and a beta shipped in 2004. Unfortunately, most of what was in Longhorn didn’t work particularly well. As the calendar rolled over into 2005, the Windows team reviewed their grandiose plans for Longhorn and scaled it back, throwing away much of the development effort and essentially restarting from scratch.

That decision, which became known as the “Longhorn reset,” was publicly revealed in an embarrassing Wall Street Journal article in 2005. "Longhorn was irredeemable ... Microsoft needed to start over."

(You can see what Longhorn was supposed to be in this gallery from Stephen Chapman.)

2006: Windows Vista stumbles out of the gate

After the Longhorn debacle, it was almost inevitable that the next release of Windows would be a more modest affair. No one expected it to be such a horrible mess.

Delay after delay had conditioned Microsoft's PC-building partners to ignore deadlines. As a result, they were unprepared for the major changes in the Windows driver model that were at the core of Windows Vista. On top of that, Microsoft had deliberately allowed some OEMs to ship with video hardware that didn't support Vista's signature Aero feature.

It was a collective failure. Microsoft delivered a messy glop of code that didn't work well until Service Pack 1, and the OEMs made the experience much worse by packing their products with performance-sapping crapware. The Vista tagline, "The Wow Starts Now," is still one of the most cringe-worthy ever.

2007: Vista's woes continue with WGA problems

Besides widespread security problems, Windows XP had been burned badly by piracy. One of the most important additions in Windows Vista was a new anti-piracy infrastructure that mixed product activation and ongoing validation to verify that an installation was valid ("Genuine," in Microsoft's curious marketing-speak).

The Windows Genuine Advantage program was an absolute mess in 2007, with many innocent customers finding themselves accused of piracy when they installed a new program or changed a hardware device. A Microsoft Knowledge Base article early in 2007 admitted: "This problem does not occur because of an issue in the installed program or device driver. This problem is caused by a system problem in Windows Vista."

By 2008, most of the user-hostile problems in WGA had been resolved and the system worked as intended. But the damage was done.

2008: Apple's 'Get a Mac' ads take dead aim at Microsoft

Apple's "Get a Mac" campaign started with TV ads in 2006, but it hit its stride in 2008 with a series of ads that mercilessly and effectively lampooned the problems of Windows Vista. One of the most direct was the "Calming Teas" ad, shown here. PC, played by John Hodgman, showed off his “Vista-stress-releasing bath salts and calming teas like Crashytime Chamomile and Raspberry Restart…”

2009: Windows 7 is the anti-Vista

In 2007, I wrote about the many problems of Windows Vista in a post titled "Vista isn't Me2, it's Win95 + 12 years." In that post, I offered a prediction: "If history repeats itself, Microsoft will release its next Vista update in 2009 or 2010, after a low-profile, secretive beta cycle, and it will be greeted as finally delivering on the promise of what Vista should have been all along."

That's pretty much exactly what happened. Under the leadership of new Windows boss Steven Sinofsky, Microsoft released Windows 7 right on schedule. OEMs were prepared this time, and there were few underlying architectural changes to cause problems. Windows 7 wasn’t perfect, but it was greatly improved over Windows Vista. And that "evolutionary" release was enough to make it one of Microsoft's biggest successes ever.

2010: Windows 7 establishes itself as an unqualified success

According to statistics from NetMarketShare, Windows 7 passed Windows Vista in usage a mere nine months after its release. Windows 7 also had the good fortune to arrive as the economy began to recover from a recession and businesses that had delayed PC upgrades began buying again. Everything looked rosy for the PC market. And then Apple introduced its iPad, which was the first shot in what would become a lengthy battle for the mobile market.

2011: Microsoft unveils its 'big bet,' Windows 8

In September 2011, Microsoft officially took the wraps off Windows 8, releasing a Developer Preview that was downloaded more than 500,000 times in the first 24 hours. It was the first public appearance of the new Metro interface. In a post at the time, I noted that Windows 8 was "full of great ideas" but also identified what turned out later to be a very big deal: "The transition between the new Start screen and the don't-call-it-legacy Windows Desktop and the new Metro style apps isn't as smooth as it could be."

Steve Ballmer had called Windows 8 a "big bet" earlier. In 2011, with Windows 7 still selling strongly, there was reason to be optimistic.

2012: Windows 8 launches

Under the leadership of Steven Sinofsky, Windows 8 marched through its milestones with precision. Microsoft delivered a Consumer Preview, a Release Preview, and then final code in a series of releases that led to a fall launch in New York City.

Shortly after that launch event, Sinofsky was gone, suddenly and unceremoniously. That turned out to be the first of many disappointments for Windows 8 in its first year, as buyers found themselves confused by the new interface, especially on conventional mouse-and-keyboard driven hardware. In a post a few months after the launch, I noted, "there’s no question that a lot of smart people have serious problems with the initial release of Windows 8."

2013: The big Windows 8.1 update brings back the Start button

One of the implicit promises of Windows 8 was that Microsoft would adopt a faster release tempo than its previous every-three-years schedule. The company delivered on that promise almost immediately, with the release of Windows 8.1 exactly one year after Windows 8. This wasn't just a service pack, either. It included major new features, including the return of the Start button.

As I noted in a first look, "This is a significant update that clearly represents much more than just a reaction to seven months’ worth of occasionally brutal customer feedback about Windows 8." The other thing that was happening at the same time was an increasing availability of touch-enabled hardware that was designed with Windows 8 in mind. Still, it's telling that "Start menu replacements" were the best-selling software products for Microsoft's new OS.

2014: A second major Windows 8 update arrives

You thought Windows 8.1 arrived quickly? A second update, adding still more features aimed at mollifying unhappy desktop users, was released roughly six months after Windows 8.1.

And at the Build 2014 developers conference, Microsoft promised that it would be restoring the Start menu and allowing "modern" (the new name for Metro) apps to run in a window. It's not exactly a retreat, because the touch-first interface is still at the core of the latest Windows. But it's a quick admission that the problems with Windows 8 will take some time to resolve completely.

And as the occasionally hostile reactions to Windows 8 make clear, the Windows monopoly on personal computing, which was powerful enough at the turn of the century to bring the full weight of the United States Government down on Microsoft, has ended.

2001: Windows XP ships

The revolutionary part of Windows XP was that it unified the business and consumer versions of Windows in a single product. The Windows NT kernel replaced the old DOS-plus-Windows hybrid that had been used in Windows 95, Windows 98, and the ill-fated Windows Millennium Edition. Business users who had adopted the NT-based Windows 2000 a year earlier saw the garish new XP interface, which was widely panned for its "Fisher-Price" appearance. In its first year on the market, XP was far from successful, with less than 10 percent of the installed base upgrading in that first year.

XP's launch event took place in a somber New York City, the month after the 9/11 attacks.

Ed Bott is an award-winning technology writer with more than two decades' experience writing for mainstream media outlets and online publications. He has served as editor of the U.S. edition of PC Computing and managing editor of PC World; both publications had monthly paid circulation in excess of 1 million during his tenure. He is the a...
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Ed Bott is a freelance technical journalist and book author. All work that Ed does is on a contractual basis.Since 1994, Ed has written more than 25 books about Microsoft Windows and Office. Along with various co-authors, Ed is completely responsible for the content of the books he writes. As a key part of his contractual relationship with publishers, he gives them permission to print and distribute the content he writes and to pay him a royalty based on the actual sales of those books. Ed's books have been distributed under several imprints: Que Publishing (a division of Pearson Education); Microsoft Press (with production and distribution by O'Reilly), and Fair Trade Digital Exchange, where he was briefly a partner. On occasion, Ed accepts consulting assignments. In recent years, he has worked as an expert witness in cases where his experience and knowledge of Microsoft and Microsoft Windows have been useful. In each such case, his compensation is on an hourly basis, and he is hired as a witness, not an advocate. Ed sometimes receive fees and/or travel expenses for live speeches and webinars from companies and organizations. Acceptance of these fees does not constitute an endorsement of the company's products. Ed does not own stock or have any other financial interest in Microsoft or any other software company. He owns 500 shares of stock in EMC Corporation, which was purchased before the company's acquisition of VMware. In addition, he owns 350 shares of stock in Intel Corporation, purchased more than seven years ago. All stocks are held in retirement accounts for long-term growth. Ed does not accept gifts from companies he covers. All hardware products he writes about are purchased with his own funds or are review units covered under formal loan agreements and are returned after the review is complete.